The 5 Worst Toronto Maple Leafs Trades or Signings Since 2000

With the trade deadline approaching, what are some Toronto Maple Leafs worst moves of the new century?

The Toronto Maple Leafs are one of the oldest and successful teams in the NHL. By successful, I mean before 1968. Anyway, not everything the team did went as planned.

Some moves looked horrid from the start, while other’s took time to reveal their negative consequences.

In honor of the upcoming trade deadline, let’s take a look at five of the worst moves the Leafs made since 2000.

Toronto Maple Leafs Sign Jeff Finger (2008)

The Leafs have a mediocre team with Hall of Famer Mats Sundin leading the way. Defenseman Thomas Kaberle is putting up more points than all but two forwards. Goaltenders Vesa Toskala and Andrew Raycroft played better on the bench than they did in the net.

Then general manager Cliff Fletcher knew he had to improve the team if the Leafs were to become competitive. To help improve the team, Fletcher looked to sign a defenseman.

Toronto couldn’t score, defend, or even hold onto the puck. To combat that, the Leafs signed defenseman Jeff Finger to a four-year contract worth $3.5 million per season.

Before arriving in Toronto, Finger played two seasons with the Colorado Avalanche. The team drafted him in the eighth round back in 1999. It took him six seasons until he played in his first NHL game. (stats from nhl.com).

Even then, the defenseman never saw the ice much. Finger played 92 games in two seasons, putting up 24 points, and was a plus 22. The argument for the signing was Finger’s defensive prowess and physicality. With the situation the Leafs were in, anyone was an upgrade. Finger looked like a decent risk to take, but not for a four-year contract.

In his new blue sweater, Finger looked like a different player, and not in a good way. He set a career-high with 23 points in 66 games one year into his new contract. The positives stop there. His inability to bring his defensive abilities to Toronto limited him to the 66 games. That would continue the following season as he played only 39 games before being waived.

From there, the defenseman played the rest of his two-year deal in the AHL and struggled to do that. He played in 23 games and 31 games, respectively.

The term “it can’t get any worse than this” was proven wrong by the Toronto Maple Leafs once again. It was a wasted signing that did not pan out at all. As bad as it sounds, it comes nowhere near the next horrifying move.

Leafs Trade for Owen Nolan (2003)

The Toronto Maple Leafs are a competitive team pushing for a playoff run. Sundin and Alexander Mogilny are leading the way, with Ed Belfour playing great in net. Head coach and general manager Pat Quinn wanted to bolster the team’s forward group. He chose to look at the failing San Jose Sharks and traded for power forward Owen Nolan.

Heading to California was Alyn McCauley, Brad Boyes, and a first-round pick. With the first-rounder, San Jose drafted defenseman Mark Stuart. In trading for Nolan, Toronto gets a big body forward to protect superstars Mogilny and Sundin while being a secondary scorer. He was the perfect addition to take the Leafs through a deep playoff run.

Nolan played very well in a Maple Leafs sweater. He picked up 12 points in 14 games following the trade and two points in seven games during the playoffs. That was followed up with 48 points in 65 regular-season games the season after.

The forward had a hard time staying on the ice due to injuries and even missed the playoffs in his second season with Toronto. After that, he took a season off from hockey after the lockout year before signing with the Pheonix Coyotes.

Boyes ended up becoming a 40-goal scorer and was a reliable secondary scorer for most of his career. He became a center the Leafs sure would have loved to have.  McCauley didn’t play in the NHL much longer after leaving Toronto. In his time with the Sharks, he was a solid third-liner that was more than reliable defensively.

The first-round pick was from the 2003 NHL Draft. That ended up being one of the deepest drafts ever, producing Eric Staal, Ryan Getzlaf, and Patrice Bergeron. Toronto would have had the opportunity to draft Bergeron, Corey Perry, or Ryan Kessler with that first-rounder.

Had Nolan stayed with Toronto and remained healthy, the deal would not have been that bad. Unfortunately, that did not end up happening. What “could have been” heavily outweighed what happened. The result of that is one of the worst trades the Leafs have ever made.

Leafs Trade for Vesa Toskala (2007)

The Toronto Maple Leafs desperately needed a goaltender. All three goalies that were on their roster had under a .900 save percentage.  It looked as if the opposing team could shoot the puck from the other side of the ice and score it. That is how bad the goaltending was. What goalie would give up such a horrifying goal?

Anyway, general manager John Ferguson Jr. wanted to shake up the NHL with a blockbuster trade. It would not only give the Leafs their starting goaltender for the foreseeable future but also a physical forward. He called the San Jose Sharks and made a trade for goaltender Vesa Toskala and forward Mark Bell. All it cost was a first and second-round pick from the 2007 draft and a fourth-rounder from the 2009 draft.

Why have the opportunity to draft Kevin Shattenkirk, Wayne Simmonds, or Mattias Ekholm when you can have Toskala? Yes, speculation surrounding “what could’ve been” at a draft is a waste of time. That doesn’t mean it won’t sting, though. Okay, I got a little sidetracked again. How exactly did the players Fergeson traded for in the blockbuster deal pan out?

Let’s start with the six-foot and four-inch-tall power forward Bell. He would play only 35 games in the ’07-’08 season before leaving in free agency that offseason. In those games, he accumulated ten points 60 penalty minutes and was a minus two.

That is okay because Toskala was the main piece of the trade anyway. He would play two seasons with the Leafs as their starter and another half of a season before being traded to the Calgary Flames.  As a Leaf, Vesa had a .894 save percentage and a 2.94 goals-against average. While the save percentage doesn’t surprise me, his GAA is better than I thought it would be.

Fergeson set the Toronto Maple Leafs back countless years with this trade alone. Not only would the draft picks help the team rebuild around their aging legend, but he could have grabbed a different goaltender.

Leafs Sign David Clarkson (2013)

We have seen countless bad trades by the Toronto Maple Leafs. It often overshadows the signings the team has made. This time around, it is a signing that stings. In his first offseason with the team, general manager Dave Nonis wanted to make a big splash in the free-agent market. I guess you can say he did exactly that.

People were pleased with the signing, despite concerns over the longevity. The player brought to Toronto was held in high regard for his rare ability to be a tough guy and a goal-scorer. That man was David Clarkson.

While his ceiling was not as high, the Leafs signed Clarkson for a similar reason they brought in Nolan ten years prior. The difference is Nolan proved himself as an offensive talent, while Clarkson had one decent season.

That season was the ’11-’12 season when he put up 30 goals and 138 penalty minutes in 80 games. Many analysts didn’t say that he had only 16 assists, bringing his points total to 46 in 80 games. His second-best offensive output was two years prior when he put up 24 points in 46 games. His ceiling was a goon that might just put up 0.5 points per game.

It was okay, though. Toronto needed a tough guy, and Clarkson just happened to have two decent seasons. That warranted him a SEVEN YEAR DEAL that would pay him $5.25 MILLION PER SEASON.  Whew, that drew a tear from me. Maybe we should look at what the hometown kid did as a Maple Leaf before we jump to conclusions, right?

In year one, Clarkson produced 11 points in 60 games.

In year two, Clarkson produced 15 points in 58 games.

Okay, let me resume my anger at Dave Nonis. ARE YOU KIDDING ME?!

With five more years left on the unbelievably laughable contract, Nonis flips him to the Columbus Blue Jackets for a player that would never play in the NHL again, Nathan Horton. Despite acquiring his contract, it would not count against the salary cap.

That was one of the worst signings in NHL history. The duration, the salary, everything about it sucked. The only positive was that there wasn’t a no-movement clause, and the Leafs found a way to move him.